Literature DB >> 25485687

Acetylation serves as a protective group in noscapine biosynthesis in opium poppy.

Thu-Thuy T Dang1, Xue Chen1, Peter J Facchini1.   

Abstract

We have characterized four sequential enzymes that transform 1-hydroxy-N-methylcanadine to narcotoline hemiacetal, completing our elucidation of noscapine biosynthesis in opium poppy. Two cytochromes P450 catalyze hydroxylations at C13 and C8 on the protoberberine scaffold, the latter step inducing ring opening and the formation of an aldehyde moiety. Acetylation at C13 before C8 hydroxylation introduces a protective group subsequently hydrolyzed by a carboxylesterase, which triggers rearrangement to a cyclic hemiacetal.

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Year:  2014        PMID： 25485687     DOI： 10.1038/nchembio.1717

Source DB:  PubMed          Journal:  Nat Chem Biol        ISSN： 1552-4450            Impact factor:   15.040


  20 in total

1.  Synergists and antagonists of mitotic poisons.

Authors:  H LETTRE
Journal:  Ann N Y Acad Sci       Date:  1954-11-17       Impact factor: 5.691

2.  Characterization of three O-methyltransferases involved in noscapine biosynthesis in opium poppy.

Authors:  Thu-Thuy T Dang; Peter J Facchini
Journal:  Plant Physiol       Date:  2012-04-25       Impact factor: 8.340

3.  Physical linkage of metabolic genes in fungi is an adaptation against the accumulation of toxic intermediate compounds.

Authors:  Kriston L McGary; Jason C Slot; Antonis Rokas
Journal:  Proc Natl Acad Sci U S A       Date:  2013-06-24       Impact factor: 11.205

4.  Biochemical conservation and evolution of germacrene A oxidase in asteraceae.

Authors:  Don Trinh Nguyen; Jens Christian Göpfert; Nobuhiro Ikezawa; Gillian Macnevin; Meena Kathiresan; Jürgen Conrad; Otmar Spring; Dae-Kyun Ro
Journal:  J Biol Chem       Date:  2010-03-29       Impact factor: 5.157

5.  Opium alkaloid noscapine is an antitumor agent that arrests metaphase and induces apoptosis in dividing cells.

Authors:  K Ye; Y Ke; N Keshava; J Shanks; J A Kapp; R R Tekmal; J Petros; H C Joshi
Journal:  Proc Natl Acad Sci U S A       Date:  1998-02-17       Impact factor: 11.205

6.  Cloning and characterization of canadine synthase involved in noscapine biosynthesis in opium poppy.

Authors:  Thu-Thuy T Dang; Peter J Facchini
Journal:  FEBS Lett       Date:  2013-12-04       Impact factor: 4.124

7.  Metabolic map and bioactivation of the anti-tumour drug noscapine.

Authors:  Zhong-Ze Fang; Kristopher W Krausz; Fei Li; Jie Cheng; Naoki Tanaka; Frank J Gonzalez
Journal:  Br J Pharmacol       Date:  2012-11       Impact factor: 8.739

8.  CYP82Y1 is N-methylcanadine 1-hydroxylase, a key noscapine biosynthetic enzyme in opium poppy.

Authors:  Thu-Thuy T Dang; Peter J Facchini
Journal:  J Biol Chem       Date:  2013-12-09       Impact factor: 5.157

Review 9.  The anti-cancer activity of noscapine: a review.

Authors:  Massoud Mahmoudian; Parvaneh Rahimi-Moghaddam
Journal:  Recent Pat Anticancer Drug Discov       Date:  2009-01       Impact factor: 4.169

10.  Morphine biosynthesis in opium poppy involves two cell types: sieve elements and laticifers.

Authors:  Akpevwe Onoyovwe; Jillian M Hagel; Xue Chen; Morgan F Khan; David C Schriemer; Peter J Facchini
Journal:  Plant Cell       Date:  2013-10-08       Impact factor: 11.277
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  21 in total

1.  Isolation and Characterization of O-methyltransferases Involved in the Biosynthesis of Glaucine in Glaucium flavum.

Authors:  Limei Chang; Jillian M Hagel; Peter J Facchini
Journal:  Plant Physiol       Date:  2015-08-21       Impact factor: 8.340

Review 2.  The Noscapine Chronicle: A Pharmaco-Historic Biography of the Opiate Alkaloid Family and its Clinical Applications.

Authors:  Padmashree C G Rida; Dillon LiVecche; Angela Ogden; Jun Zhou; Ritu Aneja
Journal:  Med Res Rev       Date:  2015-07-14       Impact factor: 12.944

3.  Purine Permease-Type Benzylisoquinoline Alkaloid Transporters in Opium Poppy.

Authors:  Mehran Dastmalchi; Limei Chang; Rongji Chen; Lisa Yu; Xue Chen; Jillian M Hagel; Peter J Facchini
Journal:  Plant Physiol       Date:  2019-08-29       Impact factor: 8.340

4.  Employing a biochemical protecting group for a sustainable indigo dyeing strategy.

Authors:  Tammy M Hsu; Ditte H Welner; Zachary N Russ; Bernardo Cervantes; Ramya L Prathuri; Paul D Adams; John E Dueber
Journal:  Nat Chem Biol       Date:  2018-01-08       Impact factor: 15.040

5.  Stereochemical inversion of (S)-reticuline by a cytochrome P450 fusion in opium poppy.

Authors:  Scott C Farrow; Jillian M Hagel; Guillaume A W Beaudoin; Darcy C Burns; Peter J Facchini
Journal:  Nat Chem Biol       Date:  2015-07-01       Impact factor: 15.040

6.  Complete biosynthesis of noscapine and halogenated alkaloids in yeast.

Authors:  Yanran Li; Sijin Li; Kate Thodey; Isis Trenchard; Aaron Cravens; Christina D Smolke
Journal:  Proc Natl Acad Sci U S A       Date:  2018-04-02       Impact factor: 11.205

7.  3'O-Methyltransferase, Ps3'OMT, from opium poppy: involvement in papaverine biosynthesis.

Authors:  Parul Agarwal; Sumya Pathak; Ravi Shankar Kumar; Yogeshwar Vikram Dhar; Ashutosh Pandey; Sudhir Shukla; Prabodh Kumar Trivedi
Journal:  Plant Cell Rep       Date:  2019-06-12       Impact factor: 4.570

8.  High-throughput metabolomic and transcriptomic analyses vet the potential route of cerpegin biosynthesis in two varieties of Ceropegia bulbosa Roxb.

Authors:  Sachin A Gharat; Balkrishna A Shinde; Ravindra D Mule; Sachin A Punekar; Bhushan B Dholakia; Ramesha H Jayaramaiah; Gopalakrishna Ramaswamy; Ashok P Giri
Journal:  Planta       Date:  2019-12-04       Impact factor: 4.116

Review 9.  Biosynthesis and synthetic biology of psychoactive natural products.

Authors:  Cooper S Jamieson; Joshua Misa; Yi Tang; John M Billingsley
Journal:  Chem Soc Rev       Date:  2021-06-21       Impact factor: 60.615

10.  Acyltransferase AniI, a Tailoring Enzyme with Broad Substrate Tolerance for High-Level Production of Anisomycin.

Authors:  Qing Wang; Lingxin Kong; Xiaoqing Zheng; Jufang Shen; Junbo Wang; Dashan Zhang; Yongjian Qiao; Jinjin Wang; Zixin Deng; Delin You
Journal:  Appl Environ Microbiol       Date:  2021-06-25       Impact factor: 4.792
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